Antiseptics



Patented May 17, 1938 UNITED STATES PATET OFFlC Eastman Kodak Company,Rochester, N. Y., a corporation of New Jersey Serial No. 114,227

No Drawing. Application December 4, 1936,

K 10 Claims.

This invention refers to antiseptics, and more particularly toantiseptics which are readily miscible with water. Its object is toprovide disper- 'sions of certain germicides, which dispersions can bereadily mixed with water to provide antiseptic solutions of good wettingpower.

It is known that certain phenolic compounds, namely ortho-phenyl phenol(HO.CeH4.CsH5) 2 :4 5-trichlorop'henol (CsH2C13.0H) monochloroortho-phenyl phenol (HQ.ClCsHa.CsH5), 3-chloro-4-hydroxy diphenyl(HO.C1C6H-3.C6H5) and 3- bromol-hydroxy diphenyl (HO.BIC6H3".C6H5), andtheir sodium salts, have germicidal properties. It is also known todisperse certain germicidal substances, such as the cresols, in soapsolutions. However, the phenolic compounds belonging to the group justenumerated cannot be dispersed directly in soap solutions.

I have discovered that the phenolic compounds belonging to the groupabove enumerated are miscible with caustic-soluble hardwood oils, andthat solutions of these phenolic compoundsin hardwood oils can bereadily incorporated in aqueous soap solutions to form dispersions whichcan be easily mixed with water to give antiseptic and fungicidalsolutions of good wetting power, even for greasy surfaces.

The caustic-soluble hardwood oils which I employ are derived from heavyhardwood oils and tars having boiling ranges from 170 C. to 310 C.

, These heavy oils and tars settle out of the raw pyroligneous' acidwhich results from the destructive distillation of hardwood, and areknown as settled tar. The caustic-soluble portion may be isolated asfollows: A 5-15% solution of sodium hydroxide is added to the hardwoodoil, with stirring, until the mixture becomes alkaline. The neutral oilsseparate out, and sodium salts of the acidic components of the wood oilare formed.

The'greater portion of the neutral oils is removed mechanically, and theremainder by steam dis-- tillation. These neutral oils are discarded.The

solution of sodium salts is then treated with car- Percent Percent 40%cocoanut oil soap emulsion 50 50 Ethyl alcohol 13 13 Caustic-solublehardwood oil 32 Phenolic compound belonging to above-enumerated group 53 Essential oil a 2 2 All proportions are given by weight. The phenoliccompound is first dissolved in the caustic-soluble hardwood oil, andthis solution is then mixed with the other ingredients. Obviously, theproportions of the ingredients may be varied widely, and I am not to belimited by the above examples except as indicated in the appendedclaims.

As much as 15% or even more of the phenolic compound may be' used. Theessential oil may be omitted if thereis no reason for improving the odorof the composition. A small amount of potassium iodide or potassiumbromide, for example 0.25 gram per 100 cc. of composition, may be addedto prevent discoloration of theantiseptic composition in the light andair, as is described, in connection with liquid, antiseptic.toilet-soap, in the copending application of Louis J. Figg, Jr. andEdward E. Shaulis, Serial No. 100,037, filed September 9, 1936.

Of all the phenolic compounds belonging to the group enumerated above, Iprefer to use monochloro ortho-phenyl phenol, because I have found thatit is the most soluble in caustic-soluble hardwood oil.

What I claim as my invention, and desire to be secured by Letters Patentof the United States is:

1. An aqueous soap dispersion comprising caustic-soluble hardwood oiland an antiseptic phenol compound selected from the group consisting ofortho-phenyl phenol, 2 :4 5-trichloro-phenol, monochloro ortho-phenylphenol, 3-chloro-4-hydroxy diphenyl, 3-bromo-4-hydroxy diphenyl, andtheir sodium salts, the caustic-soluble hardwood oil acting as adispersing agent for the antiseptic phenol compound.

2. An aqueous soap dispersion comprising caustic-soluble hardwood oiland monochloro orthophenyl phenol, the caustic-soluble hardwood oilacting as a dispersing agent for the'monochloroortho-phenyl phenol.

3. Process of preparing an aqueous soap dispersion of an antisepticphenol compound selected from the group consisting of ortho-phenylphenol, 2:4:5-trichlorophenol, monochloro orthophenyl phenol,3-chloro-4-hydroxy diphenyl, 3- bromo-4-hydroxy diphenyl, and theirsodium salts, which comprises dissolving the antiseptic phenol compoundin caustic-soluble hardwood oil and dispersing the resulting solution inan aqueous soap emulsion.

4. Process of preparing an aqueous soap dispersion of monochloroortho-phenyl phenol, which comprises dissolving the monochloroorthophenyl phenol in caustic-soluble hardwood oil and dispersing theresulting solution in an aqueous soap emulsion.

5. An aqueous soap dispersion comprising caustic-soluble hardwood oil,an antiseptic phenol compound selected from the group consisting ofortho-phenyl phenol, 2 4 :5-trichloro-pheno1, monochloro ortho-phenylphenol, 3-chloro-4- hydroxy diphenyl, 3-bromo-4-hydroxy diphenyl, andtheir sodium salts. and a sufficient quantity of a potassium halideselected from the group consisting of potassium bromide and potassiumiodide to keep the dispersion from darkening in the light and air. I

6. -An aqueous soap dispersion comprising caustic-soluble hardwood oil,monochloro ortho-phenyl phenol, and a sufilcient quantity of a potassiumhalide selected from the group consisting of potassium bromide andpotassium iodide to keep the dispersion from darkening in the light andair.

7. An aqueous soap dispersion comprising caustic-soluble hardwood 011,an antiseptic phenol compound selected from the group consisting ofortho-phenyl phenol, 2:4:5 trichlorophenol,

20 monochloro ortho-phenyl phenol, 3-ch1oro-4-hydroxy diphenyl,3-bromo-4-hydroxy diphenyl, and their sodium salts, and approximately0.25 gram, per 100 cubic centimeters, of a potassium halide selectedfrom the group consisting of potassium bromide and potassium iodide. j

8. An aqueous soap dispersion comprising caustic-soluble hardwood oil,monochloro ortho-phenyl phenol, and approximately 0.25 gram, per 100cubic centimeters, of a potassium halide selected from the groupconsisting of potassium bromide and potassium iodide.

9. A solution, in caustic-soluble hardwood oil, of an antiseptic phenolcompound selected from the group consisting of ortho-phenyl phenol, 2 4fi-trichloro-phenol, monochloro ortho-phenyl phenol, 3-chloro-4-hydroxydiphenyl, 3-bromo-4- hydroxy diphenyl, and their sodium salts.

10. A vsolution of monochloro ortho-phenyl phenol in caustic-solublehardwood oil.

LOUIS J. FIGG, JR'..

